W. Neish
Sep 2, 2010
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Journal
Recueil des Travaux Chimiques des Pays-Bas
Abstract
2-methoxy- and 3-methoxy-9-aminofluorene have been prepared. Their reactions with ethyl chloroformate, maleic anhydride and carbon dioxide are described and similar reactions have been studied with the parent base, 9-aminofluorene. These reactions lead to the formation of N-carbethoxy derivatives, 9-maleamic acids and substituted ammonium carbamates respectively. Attempts to obtain the 9-amino derivatives by reduction of the oximes with sodium amalgam in alcohol-acetic acid medium were unsuccessful. In each case, the corresponding fluorene derivative was obtained. Thus the hitherto undescribed 3-methoxyfluorene has been prepared. 2-Methoxy- and 3-methoxy-9-aminofluorene hydrochlorides produce local anaesthesia of the tongue and of guinea pig skin, the former action having been noted by Nakamura for 9-aminofluorene hydrochloride. Kymograph studies with the above mentioned amines indicate that stimulation or relaxation of the contracting pregnant rat uterus may be obtained depending on the concentrations employed. These effects are reversible. Inhibition of contraction but no stimulation was noted with a non-pregnant rat uterus. Data concerning the effects of related compounds including 2-amino-hydrochloride on uterine contraction are presented.